Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:36:49 UTC
Update Date2022-03-07 02:53:52 UTC
HMDB IDHMDB0033840
Secondary Accession Numbers
  • HMDB33840
Metabolite Identification
Common NameDihydro-5-methyl-2(3H)-furanone
DescriptionDihydro-5-methyl-2(3H)-furanone, also known as 4-hydroxypentanoic acid lactone or 4-methyl-gamma-butyrolactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, dihydro-5-methyl-2(3H)-furanone is considered to be a fatty ester lipid molecule. Dihydro-5-methyl-2(3H)-furanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1563862469
Synonyms
ValueSource
4-Hydroxypentanoic acid lactoneChEBI
4-Hydroxyvaleric acid lactoneChEBI
4-Methyl-4-hydroxybutanoic acid lactoneChEBI
4-Methyl-gamma-butyrolactoneChEBI
4-PentanolideChEBI
4-ValerolactoneChEBI
gamma-PentalactoneChEBI
gamma-PentanolactoneChEBI
4-Hydroxypentanoate lactoneGenerator
4-Hydroxyvalerate lactoneGenerator
4-Methyl-4-hydroxybutanoate lactoneGenerator
4-Methyl-g-butyrolactoneGenerator
4-Methyl-γ-butyrolactoneGenerator
g-PentalactoneGenerator
Γ-pentalactoneGenerator
g-PentanolactoneGenerator
Γ-pentanolactoneGenerator
g-ValerolactoneHMDB
Γ-valerolactoneHMDB
Dihydro-5-methyl-2(3H)-furanoneChEBI
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name5-methyloxolan-2-one
Traditional Namegamma-valerolactone
CAS Registry Number57129-69-8
SMILES
CC1CCC(=O)O1
InChI Identifier
InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
InChI KeyGAEKPEKOJKCEMS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-31 °CNot Available
Boiling Point207.00 to 208.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility93810 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.270The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility92.6 g/LALOGPS
logP0.36ALOGPS
logP0.57ChemAxon
logS-0.03ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.73 m³·mol⁻¹ChemAxon
Polarizability10.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.34131661259
DarkChem[M-H]-113.37831661259
DeepCCS[M+H]+126.38130932474
DeepCCS[M-H]-124.48530932474
DeepCCS[M-2H]-160.11330932474
DeepCCS[M+Na]+134.5230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydro-5-methyl-2(3H)-furanoneCC1CCC(=O)O11580.6Standard polar33892256
Dihydro-5-methyl-2(3H)-furanoneCC1CCC(=O)O1869.8Standard non polar33892256
Dihydro-5-methyl-2(3H)-furanoneCC1CCC(=O)O1961.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dihydro-5-methyl-2(3H)-furanone EI-B (Non-derivatized)splash10-056u-9000000000-7c79f68cacbc95c0ea482017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydro-5-methyl-2(3H)-furanone EI-B (Non-derivatized)splash10-056u-9000000000-7c79f68cacbc95c0ea482018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-5-methyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9000000000-6c4e9500ba034d9524ae2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-5-methyl-2(3H)-furanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6u-9000000000-9d68020f06bf659a559b2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 10V, Positive-QTOFsplash10-0udi-3900000000-2daa06af8bff34a31a4f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 20V, Positive-QTOFsplash10-0udi-9500000000-f8a8c8887cd21f939e432016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 40V, Positive-QTOFsplash10-052f-9000000000-e9d8edd5c37160a8ed5e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 10V, Negative-QTOFsplash10-0002-9000000000-6b4c492a247987f111772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 20V, Negative-QTOFsplash10-052b-9000000000-c3119840ef26293d0add2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 40V, Negative-QTOFsplash10-0006-9000000000-2fafb85814b3a8bd32672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 10V, Negative-QTOFsplash10-0a4j-9000000000-932824495d928b5c87242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 20V, Negative-QTOFsplash10-0005-9000000000-3c1929af1b77d9f5776d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 40V, Negative-QTOFsplash10-0bu0-9000000000-f1d4f2200040f212d7542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 10V, Positive-QTOFsplash10-0a4i-9100000000-6dc4e2799b890bac71862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 20V, Positive-QTOFsplash10-0a4i-9000000000-cb98e64a6fd6dbe952fd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-5-methyl-2(3H)-furanone 40V, Positive-QTOFsplash10-0a4u-9000000000-db3920c5b5d7b931f3772021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012014
KNApSAcK IDC00055472
Chemspider ID7633
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Valerolactone
METLIN IDNot Available
PubChem Compound7921
PDB IDNot Available
ChEBI ID48569
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1024031
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .